IP Library Granted Patent US 11,239,426
Granted Patent B2
US 11,239,426 · App. 16/463,184 · Granted Feb 1, 2022

Electroactive compounds

Inventors: Hjalti Skulason (Buellton, CA); Viacheslav V. Diev (Wilmington, DE); Giang Dong Vo (Wilmington, DE); Weiying Gao (Landenberg, PA); Weishi Wu (Landenberg, PA); Norman Herron (Newark, DE); Michael Henry Howard, Jr. (Montchanin, DE); Kalindi Dogra (Wilmington, DE); Yunlong Zou (Wilmington, DE)
H01L51/0061C07C211/61C07D487/04C07D493/04C07D493/14C09K11/06H01L51/006C07C2603/54C09K2211/1007C09K2211/1014C09K2211/1018H01L51/0054H01L51/0056H01L51/0058H01L51/0072H01L51/0073H01L51/5012
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Quick Facts
Patent No.
US 11,239,426
App. No.
16/463,184
Granted
Feb 1, 2022
Kind
B2
Abstract

There is provided a compound having Formula (I), Formula (II), or Formula (III). The variables are described in detail herein.

Claims (50)

1. A compound having Formula I

wherein:

Ar 1 -Ar 6 are the same or different and are selected from the group consisting of hydrocarbon aryl groups, heteroaryl groups, and substituted derivatives thereof;

a and b are the same or different and are 0 or 1;

m and n are 1; and

Core is Formula IB or Formula IC

where:

Y is the same or different at each occurrence and is selected from the group consisting of O, S, Se, Te, NR 2 , CR 3 R 4 , and SiR 5 R 6 ;

R 2 is the same or different at each occurrence and is selected from the group consisting of alkyl, hydrocarbon aryl, heteroaryl, and substituted derivatives thereof;

R 3 -R 6 are the same or different at each occurrence and are selected from the group consisting of alkyl, silyl, germyl, hydrocarbon aryl, heteroaryl, and substituted derivatives thereof, where R 3 and R 4 and/or R 5 and R 6 can be joined to form a cyclic group selected from the group consisting of cycloalkyl, silacycloalkyl, spirofluorenyl, silaspirofluorenyl, or a substituted derivative thereof;

a1 and b1 are the same or different and are 0 or 1;

a double dashed line between two rings indicates that the rings are fused together in any orientation;

* indicates a point of attachment in the identified formula; and

# and ## represent no bond or a point of attachment in the identified formula, such that when a1=0 then # is a point of attachment, when a1=1 then # is no bond, when b1=0 then ## is a point of attachment, and when b1=1 then ## is no bond;

and further wherein the Core may have one or more substituents selected from the group consisting of D, alkyl, silyl, germyl, hydrocarbon aryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated germyl, deuterated hydrocarbon aryl, and deuterated heteroaryl.

2. The compound of claim 1 , wherein the Core is selected from the group consisting of Formula IB-1 through Formula IB-m

where:

R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, CN, alkyl, alkoxy, fluoroalkyl, hydrocarbon aryl, aryloxy, heteroaryl, silyl, siloxane, siloxy, germyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated alkoxy, deuterated hydrocarbon aryl, deuterated aryloxy, deuterated heteroaryl, deuterated heteroaryl deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl;

w is an integer from 0 to a maximum number of bonding positions available.

3. The compound of claim 1 , wherein the Core is selected from the group consisting of Formula IB-aa through Formula IB-mm

where:

Y 1 through Y 5 are the same or different and are selected from the group consisting of O, S, Se, Te, NR 2 , CR 3 R 4 , and SiR 5 R 6 , wherein at least one of Y 1 through Y 5 is different from the other Y 1 through Y 5 groups;

R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, CN, alkyl, alkoxy, fluoroalkyl, hydrocarbon aryl, aryloxy, heteroaryl, silyl, siloxane, siloxy, germyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated alkoxy, deuterated hydrocarbon aryl, deuterated aryloxy, deuterated heteroaryl, deuterated heteroaryl deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl; and

w is an integer from 0 to a maximum number of bonding positions available.

4. The compound of claim 1 , wherein the Core is selected from the group consisting of Formula IC-a through IC-p

where:

R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, CN, alkyl, alkoxy, fluoroalkyl, hydrocarbon aryl, aryloxy, heteroaryl, silyl, siloxane, siloxy, germyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated alkoxy, deuterated hydrocarbon aryl, deuterated aryloxy, deuterated heteroaryl, deuterated heteroaryl deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl;

e and f are the same or different and are an integer of 0-5; and

g is an integer of 0-2.

5. The compound of claim 4 , wherein the Core is selected from the group consisting of Formula IC-a1 and Formula IC-a2

6. A compound having Formula II or Formula III

wherein:

Ar 1 -Ar 8 are the same or different and are selected from hydrocarbon aryl groups, heteroaryl groups, and substituted derivatives thereof;

R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, CN, alkyl, alkoxy, fluoroalkyl, hydrocarbon aryl, aryloxy, heteroaryl, silyl, siloxane, siloxy, germyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated alkoxy, deuterated hydrocarbon aryl, deuterated aryloxy, deuterated heteroaryl, deuterated heteroaryl, deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl;

R 2a and R 2b are the same or different and are selected from the group consisting of H, D, F, CN, alkyl, alkoxy, fluoroalkyl, hydrocarbon aryl, aryloxy, heteroaryl, silyl, siloxane, siloxy, germyl, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated alkoxy, deuterated hydrocarbon aryl, deuterated aryloxy, deuterated heteroaryl, deuterated heteroaryl, deuterated silyl, deuterated siloxane, deuterated siloxy, and deuterated germyl;

Q is selected from the group consisting of naphthodifuran, Formula IA, Formula IB and Formula IC:

wherein:

Y is the same or different at each occurrence and is selected from the group consisting of O, S, Se, Te, NR 2 , CR 3 R 4 , and SiR 5 R 6 ;

R 2 is the same or different at each occurrence and is selected from the group consisting of alkyl, hydrocarbon aryl, heteroaryl, and substituted derivatives thereof;

R 3 -R 6 are the same or different at each occurrence and are selected from the group consisting of alkyl, silyl, germyl, hydrocarbon aryl, heteroaryl, and substituted derivatives thereof, where R 3 and R 4 and/or R 5 and R 6 can be joined to form a cyclic group selected from the group consisting of cycloalkyl, silacycloalkyl, spirofluorenyl, silaspirofluorenyl, or a substituted derivative thereof;

a1 and b1 are the same or different and are 0 or 1;

a double dashed line between two rings indicates that the rings are fused together in any orientation;

* indicates a point of attachment in the identified formula;

# and ## represent no bond or a point of attachment in the identified formula, such that when a1=0 then # is a point of attachment, when a1=1 then # is no bond, when b1=0 then ## is a point of attachment, and when b1=1 then ## is no bond;

a, a2, b, and b2 are the same or different and are 0 or 1;

c and d are the same or different and are an integer of 0-3; and

e and f are the same or different and are an integer of 0-5.

7. An organic electronic device comprising a first electrical contact, a second electrical contact and a photoactive layer therebetween, wherein the photoactive layer comprises a compound according to claim 1 .

8. The compound of claim 1 , wherein the compound is any one selected from the group consisting of

9. The compound of claim 8 , wherein the compound is any one selected from the group consisting of

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 9, 2019
From: SKULASON, HJALTI; DIEV, VIACHESLAV V.; VO, GIANG DONG; GAO, WEIYING; WU, WEISHI; HERRON, NORMAN; HOWARD, JR., MICHAEL HENRY; DOGRA, KALINDI; ZOU, YUNLONG
To: LG CHEM, LTD.
Reel/Frame 049700/0431 →
Continuity (2)
Provisional Application 62425937 · Nov 23, 2016
Related Publication 20190378992A1 · Dec 12, 2019
Cited By (2)
US 12,421,202 US 12,660,499